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Synthesis method of six-membered ring benzylamine compound

The technology of a six-membered ring benzylamine and a synthesis method is applied in the field of organic compound synthesis, and can solve the problems of complicated synthesis process, high synthesis cost, low yield and the like, and achieve the effects of simplifying process steps, improving reaction yield and high safety factor.

Pending Publication Date: 2022-03-22
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Six-membered ring benzylamine compounds have broad application prospects as pharmaceutical intermediates. However, in related technologies, Grignard reagents are usually used as raw materials to synthesize such compounds. The synthesis methods are limited, and the synthesis cost is high and the synthesis process is cumbersome. Industrial production
Among them, polyphosphoric acid and 1-(3-fluorophenyl)cyclohexanecarbonitrile need to be reacted at a high temperature of 110°C, and the post-treatment operation is cumbersome, and it needs to be quenched with aqueous sodium bicarbonate solution, and there are continuous bubbles during the quenching process. produced, and the yield of the reaction is low, so it is not suitable to be put into industrialized production

Method used

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  • Synthesis method of six-membered ring benzylamine compound
  • Synthesis method of six-membered ring benzylamine compound
  • Synthesis method of six-membered ring benzylamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A kind of synthetic method of 1-(3-fluorophenyl) cyclohexylamine, reaction equation is as follows:

[0060]

[0061] Raw materials used in Table 1 Embodiment 1 and their charging amount

[0062] Reagent molecular formula molecular weight Feeding amount 3-fluorophenylacetonitrile C 8 h 6 FN

135.14 100g Potassium tert-butoxide C 4 h 9 KO

112.21 174.4g 1,5-Dibromopentane C 5 h 10 Br 2

229.94 170.2g potassium carbonate K 2 CO 3

138.21 186g hydrogen peroxide h 2 o 2

34.01 100ml Saturated sodium hypochlorite solution NaClO 74.44 50ml

[0063] Include the following steps:

[0064] P1. Weigh 100g of 3-fluorophenylacetonitrile into a three-necked flask, add 500ml of dimethyl sulfoxide to dissolve, cool the solution to 0°C in an ice-water bath, stir at a rate of 800r / min until the reaction is complete, add Potassium tert-butoxide 174.4g, 170.2g of 1,5-dibromopentane was ad...

Embodiment 2

[0071] A kind of synthetic method of 1-phenylcyclohexylamine, reaction equation is as follows:

[0072]

[0073] Raw material used in table 2 embodiment 2 and charging amount thereof

[0074] Reagent molecular formula molecular weight Feeding amount Phenylacetonitrile C 8 h 6 FN

117.15 10g Potassium tert-butoxide C 4 h 9 KO

112.21 20.1g 1,5-Dibromopentane C 5 h 10 Br 2

229.94 19.62g potassium carbonate K 2 CO 3

138.21 20.3g hydrogen peroxide h 2 o 2

34.01 10ml Saturated sodium hypochlorite solution NaClO 74.44 5ml

[0075] Include the following steps:

[0076] P1. Weigh 10g of phenylacetonitrile into a three-necked flask, add 50ml of dimethyl sulfoxide to dissolve, cool the solution to 0°C in an ice-water bath, stir at a speed of 600r / min until the reaction is complete, and add tert-butanol Potassium 20.1g, drop 19.62g of 1,5-dibromopentane at a rate of 1ml / min, control...

Embodiment 3

[0083] A kind of synthetic method of 1-Boc-4-phenyl-4-piperidinamine, reaction equation is as follows:

[0084]

[0085] Raw material used in table 3 embodiment 3 and its charging amount

[0086] Reagent molecular formula molecular weight Feeding amount Phenylacetonitrile C 8 h 6 FN

117.15 50g Potassium tert-butoxide C 4 h 9 KO

112.21 100.5g N-Boc-N,N-bis(2-bromoethyl)amine C 9 h 17 Br 2 NO 2

331.04 141.3g potassium carbonate K 2 CO 3

138.21 91.7g hydrogen peroxide h 2 o 2

34.01 50ml Saturated sodium hypochlorite solution NaClO 74.44 35ml

[0087] Include the following steps:

[0088] P1. Weigh 50g of phenylacetonitrile into a three-necked flask, add 250ml of dimethyl sulfoxide to dissolve, cool the solution to 0°C in an ice-water bath, stir at a speed of 800r / min until the reaction is complete, and add tert-butanol Potassium 100.5g, add 141.3g of N-Boc-N,N-bis(2-brom...

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Abstract

The invention relates to the field of synthesis of organic matters, and particularly discloses a synthesis method of a six-membered ring benzylamine compound, which comprises the following steps: taking a compound D, a compound E and potassium tert-butoxide as raw materials, taking dimethyl sulfoxide as a solvent, reacting at 5-10 DEG C for 1-2 hours, heating to 20 DEG C, reacting, and purifying and separating after the reaction is finished to obtain a compound A; the method comprises the following steps: by taking a compound A, potassium carbonate and hydrogen peroxide as raw materials and dimethyl sulfoxide as a solvent, reacting at 50-65 DEG C, adding ice water to separate out a product after the reaction is finished, filtering and washing to obtain a compound B; dissolving the compound B in acetonitrile, adjusting the pH value to 13-14, adding a saturated sodium hypochlorite solution for reaction, and purifying and washing after the reaction is finished to obtain a compound C; the method has the effect of improving the defect that the synthesis process of the six-membered ring benzylamine compound is not suitable for industrial production.

Description

technical field [0001] The present application relates to the field of organic synthesis, in particular to a method for synthesizing six-membered ring benzylamine compounds. Background technique [0002] The six-membered ring benzylamine compound refers to a class of benzylamine compound with a six-membered heterocyclic ring or a six-membered carbocyclic ring on the molecular chain in addition to the benzene ring. The six-membered ring benzylamine compound and its derivatives are the core core of the HDAC6 inhibitor ACY-775, which is used to treat malignant tumors and has a significant effect on increasing IC50. In addition, the six-membered cyclobenzylamine compounds can also be used to prevent diseases with pathological characteristics of metabolic pathways, such as cardiovascular diseases, Alzheimer's disease, and the like. [0003] Six-membered ring benzylamine compounds have broad application prospects as pharmaceutical intermediates. However, in related technologies, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/58C07C209/84C07C211/40C07C213/02C07C213/10C07C217/74C07C231/06C07C233/58C07C235/40C07C253/30C07C255/46C07D211/58C07D309/14
CPCC07C209/58C07C209/84C07C213/02C07C213/10C07C231/06C07C253/30C07D211/58C07D309/14C07C2601/14C07C255/46C07C233/58C07C211/40C07C217/74
Inventor 谢应波张庆张华罗桂云曹云程德豪
Owner 上海泰坦科技股份有限公司